Unusual asymmetry in halobenzenes, a solid-state, gas-phase and theoretical investigation

作者：Masters Sarah L^*; Mackie Iain D; Wann Derek A; Robertson Heather E; Rankin David W H; Parsons Simon

来源：Structural Chemistry, 2011, 22(2): 279-285.

DOI：10.1007/s11224-010-9700-0

• Gas electron diffraction
• Ab initio methods
• Halobenzenes

The molecular structures of 1-Br-4-F-C(6)H(4) and 1-Cl-4-F-C(6)H(4) have been studied in the gas phase using gas electron diffraction (GED) and ab initio methods. The structure of 1-Cl,4-F-C(6)H(4) in the crystalline phase has also been studied, but whilst the gaseous structures were found to possess C (2v) symmetry, the solid-state structure was found to be quite distorted, with three molecules in the asymmetric unit. These fragments only possess C (s) symmetry in the plane of the molecules, as opposed to the C (2v) symmetry observed in the gas phase. The bonding motifs within the solid-state structure are very unusual and unexpected, with quite different C-F bond lengths for the three moieties, and are a result of weak hydrogen-halogen interactions within the structure.

• 出版日期2011-4